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Bioorganic and Medicinal Chemistry Letters
Volumn 5, Issue 11, 1995, Pages 1171-1176
2,4,5- triarylimidazole inhibitors of IL-1 biosynthesis
Author keywords

[No Author keywords available]
Indexed keywords

2,4,5 TRIPHENYLIMIDAZOLE DERIVATIVE; 6 (4 FLUOROPHENYL) 2,3 DIHYDRO 5 (4 PYRIDYL)IMIDAZO[2,1 B]THIAZOLE; 6,7 DIHYDRO 2 [4 (METHYLSULFINYL)PHENYL] 3 (4 PYRIDYL) 5H PYRROLO[1,2 A]IMIDAZOLE; 6,7 DIHYDRO 2 [4 (METHYLTHIO)PHENYL] 3 (4 PYRIDYL) 5H PYRROLO[1,2 A]IMIDAZOLE; IMIDAZOLE DERIVATIVE; INTERLEUKIN 1; LIPOXYGENASE; NONSTEROID ANTIINFLAMMATORY AGENT; UNCLASSIFIED DRUG;
EID: 0029042823     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(95)00189-Z     Document Type: Article
Times cited : (136)
References (28)
  • 10
    • 0026196042 scopus 로고
    • The small molecule inhibitors of IL-1 synthesis or release which possess anti-inflammatory and/or antiarthritic activity include: Tenidap, IX 207-887
    • (1991) Cytokine , vol.3 , Issue.4 , pp. 277
    • Otterness1    Bliven2    Downs3    Natoli4    Hanson5
  • 12
    • 0025929409 scopus 로고
    • None of these molecules are selective cytokine inhibitors and, consequently, the role of cytokine inhibition in the anti-inflammatory activity is unclear.
    • (1991) Agents Actions Suppl. , vol.32 , pp. 225
    • Goto1    Chiba2    Hashida3    Shirota4
  • 13
    • 84921194260 scopus 로고    scopus 로고
    • Synergen announcement 8-Nov-1993.
  • 17
    • 84921194259 scopus 로고    scopus 로고
    • The requirement of this relationship between the pyridine and unalkyated imidazole nitrogen for IL-1 inhibitory activity was established by Dr. Paul Bender. The difference in activity between SK&F 86002 and its regioisomer SK&F 86055 is the only published account of this observation (see ref. 13).
  • 18
    • 0024334525 scopus 로고
    • 4 production and inhibition of IL-1 in human monocytes. Nevertheless, a variety of 5-lipoxygenase inhibitors and general antioxidants have been shown to inhibit IL-1 production (see ref. 13 and references therein). It has also been recently reported that certain 5-lipoxygenase inhibitors regulate IL-1 levels in synovial tissues
    • (1989) Agents Actions , vol.27 , Issue.3-4 , pp. 280
    • Lee1
  • 20
    • 84921194258 scopus 로고    scopus 로고
    • 19 Stannylation at C-5 was accomplished by deprotonating with n-butyllithium followed by quenching with tributyltin chloride. The pyrimidine moiety was introduced via a palladium catalysed coupling of 4-iodo-2-(methylthio)pyrimidine (Majeed, A. J.; Antonsen, O.; Benneche, T.; Undheim, K. Tetrahedron1989, 45, 4), 993) with the stannylated imidazole derivative. Oxidation with m-CPBA afforded the bis-sulfone which upon heating with concentrated ammonium hydroxide in a sealed vessel at 150°C gave a mixture of the desired aminopyrimidine 60 and the corresponding pyrimidone. Pyridination at C-5 using the procedure described by Lantos et al. (J. Org. Chem.1988, 53, 4223) for the synthesis of SK&F 86002 [[Truncated]]
  • 21
    • 84921194257 scopus 로고    scopus 로고
    • Fitzi, K. U. S. Patent 3,940,486, 1974.
  • 26
    • 84921194256 scopus 로고    scopus 로고
    • The effects of sterics and polarity at the 4-position was studied in detail in the pyrroloimidazole and imidazothiazole series. For example, the 4-fluoro derivative, SK&F 86002, is greater than five times more active that the 4-methylthio derivative, SK&F 105561, and the more polar 4-methylsulfinyl derivative, SK&F 105809, is inactive (see ref. 13).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.